Vacation rentals in Islamorada

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Top-rated vacation rentals in Islamorada

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Islamorada

4.95 out of 5 average rating, 40 reviews

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Sep. 22 – 29

$664 CAD per night

Guest favourite

Home in Islamorada

4.94 out of 5 average rating, 16 reviews

3 Lux Ensuites Walk/Boat Island!

Dive into the heart of Islamorada and COUPLES Imagine: THREE MASTER BEDROOMS, so no squabbles over only 1 Master! This 2017 townhome promises restful nights and lively marine filled mornings. From your balcony, salute serenity; Dockside bid sunsets a farewell or mingle with manatees and lobsters. A stroll away: world-class dining, boutiques, bars or a Paddleboard escapade. Welcome to bayside luxury with a splash of fun! Explore the community & nearby libations. Your tranquil Bayside haven awaits

Feb. 22 – Mar. 1

$897 CAD per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul. 4 – 11

$347 CAD per night

Superhost

Cottage in Islamorada

4.81 out of 5 average rating, 142 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Sep. 12 – 19

$281 CAD per night

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 164 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Dec. 7 – 14

$418 CAD per night

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 325 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Jan. 8 – 15

$295 CAD per night

Guest favourite

Apartment in Key Largo

4.92 out of 5 average rating, 228 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Aug. 22 – 29

$286 CAD per night

Guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

May 25 – Jun. 1

$312 CAD per night

Guest favourite

Home in Key Largo

4.99 out of 5 average rating, 74 reviews

Little Cottage on an island

Very nice quiet neighborhood. Clean updated home with new appliances. Owner does live on property. There is a shared washer/dryer outside. The house is fully furnished with a queen bed and pullout sofa bed twin size. The home has a beautiful little office to work in and a full kitchen with all dishes and cooking utensils. Centrally located in Key Largo... 1 mile away from everything you need! There is a 21 yrs and over policy - house does have liquor bar. Thank you! 🏝️😊

Jul. 22 – 29

$270 CAD per night

Guest favourite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Key Lime Cottage 2br 1ba w/pool

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Oct. 27 – Nov. 3

$595 CAD per night

Guest favourite

Bungalow in Islamorada

4.97 out of 5 average rating, 29 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Castaway Island! Luxury In paradise! This hidden gem is your piece of paradise waiting! Fully remodeled and furnished from the floor up. All new furniture, fixtures and furnishings await. One of the most well appointed and private Bungalows in Islamorada. Perfect for the honeymooners and special occasion couples and small families. Private outside spaces. 4 Bikes, 2 ultra lite SUP's, 2 Kayaks, 4+ beach chairs, ice chests and more await you.

Feb. 4 – 11

$1,207 CAD per night

Guest favourite

Guesthouse in Key Largo

4.91 out of 5 average rating, 188 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Sep. 23 – 30

$313 CAD per night